Synthesis of 2-Alkylidenethietanes and the transformation to Thiophenes
During the course of study on the nucleophilic substitution reaction at an sp2 carbon in the Narasaka group, a unique four-membered ring formation was realized by intramolecular nucleophilic vinylic substitution of a thiolate moiety. To generalize this 2-alkylidenethietane formation and to get mo...
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| Format: | Theses and Dissertations |
| Language: | English |
| Published: |
2009
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| Subjects: | |
| Online Access: | http://hdl.handle.net/10356/14732 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | During the course of study on the nucleophilic substitution reaction at an sp2
carbon in the Narasaka group, a unique four-membered ring formation was realized by
intramolecular nucleophilic vinylic substitution of a thiolate moiety.
To generalize this 2-alkylidenethietane formation and to get more mechanistic
information, synthesis of 2-alkylidenethietanes were examined by using this newly
developed synthetic methodology.
It was found that 2-alkylidenethietanes were oxidized to 2-alkylidenethietan-
1-oxides by treatment with m-CPBA, which has a unique structure with a strained
four-membered ring, an exo double bond, and a sulfinyl group. Accordingly, the
transformation of 2-alkylidenethietan-1-oxides were investigated. Incidentally, it
was discovered that the treatment of 2-alkylidenethietan-1-oxides with
p-toluenesulfonic acid afforded the unexpected thiophenes. The thiophene formation
was extensively studied in this MSc’s thesis. |
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